Microbicidal compositions based on dibromo-thiophene-carboxylic acid derivatives

ABSTRACT

New microbicidal compositions based on dibromo-thiophene-carboxylic acid derivatives which are known in some cases, of the formula ##STR1## in which R represents the groups --XR 1 , --NR 2  R 3 , --NR 4  OR 5  or --NR 4  --N(R 5 ) 2 , where 
     X represents oxygen or sulphur and 
     R 1 , R 2 , R 3 , R 4  and R 5  have the meanings indicated in the description, and the use of these substances for controlling undesired microorganisms. 
     New dibromo-thiophene-carboxylic acid derivatives of the formula ##STR2## in which R 9  represents the groups --SR 1 , --OR 10 , ##STR3## in which R 1 , R 4 , R 5 , R 10 , R 11 , R 12  and R 13  have the meaning indicated in the description, and processes for the preparation of the substances of the formula (I-A).

This application is a 371 of PCT/EP95/01173 Mar. 29, 1995.

The present invention relates to novel microbicidal compositions basedon dibromothiophene-carboxylic acid derivatives which are known in somecases, and the use of these substances for controlling undesiredmicroorganisms. Additionally, the invention also relates to newdibromo-thiophene-carboxylic acid derivatives and a plurality ofprocesses for their preparation.

It has already been disclosed that certain halogenothiophene-carboxamidederivatives can be employed for controlling plant diseases (cf. EP-OS 0450 355). The activity of these previously known compounds, however, isnot completely satisfactory in all fields of application, in particularat low application rates.

Furthermore, certain 4,5-dibromo-thiophene-2-carboxylic acid derivativesare known, such as, for example, the compounds4,5-dibromo-thiophene-2-carboxylic acid methyl ester (CA Reg. No.62224-24-2) and ethyl ester (CA Reg. No. 62224-25-3) and1,1-dimethylethyl ester (CA Reg. No. 62224-26-4) and 2-propinyl ester(CA Reg. No. 116 041-66-8) and 1-methyl-2-propinyl ester (CA Reg. No.131 818-24-1) and 3-butinyl ester (CA Reg. No. 131 818-21-8) andN,N-dimethylamide (CA Reg. No. 111 859-96-2) and N-ethoxy-amide (CA Reg.No. 131 818-25-2) and also 4,5-dibromothiophene-2-carboxylic acid (CAReg. No. 6324-10-3) and -carboxamide (Beilstein Reg. No. 129 357).

To date, nothing is known about fungicidal activity of these compounds.

It has now been found that the dibromo-thiophene-carboxylic acidderivatives, which are known in some cases, of the formula ##STR4## inwhich R represents the groups --XR¹, --NR² R³, --NR⁴ OR⁵ or --NR⁴--N(R⁵)₂, where

X represents oxygen or sulphur,

R¹ represents hydrogen, or straight-chain or branched alkyl which can besubstituted by halogen, cyano, amino, hydroxyl, mercapto, carboxyl,nitro, alkoxy, alkylthio, alkoxycarbonyl and/or the group ##STR5## or R¹represents optionally substituted alkenyl or optionally substitutedalkinyl, or

R¹ represents cycloalkyl or cycloalkylalkyl, each of which is optionallysubstituted, tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, each of which is optionally substituted, and aryl,aralkyl, hetaryl or hetarylalkyl, each of which is optionallysubstituted,

R² and R³ are identical or different and represent hydrogen, or alkylwhich can be substituted by halogen, cyano, amino, hydroxyl, mercapto,nitro, alkoxy, alkylthio and/or the group ##STR6## or represent alkenylwhich is optionally substituted by halogen, or alkinyl which isoptionally substituted by halogen, or

represent cycloalkyl or cycloalkylalkyl, where each of these radicalscan be substituted by alkyl, halogen, halogenoalkyl, cyano,alkylenedioxo, cycloalkyl which is optionally substituted by alkyl,and/or by optionally substituted phenyl, or

represent tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, each of which is optionally substituted, andoptionally substituted aralkyloxy,

R³ additionally represents hetaryl or hetarylalkyl, each of which isoptionally substituted,

R² and R³ furthermore together represent divalent alkanediyl, it beingpossible for a CH₂ group to be replaced by O, S or NR⁶,

R⁴ and R⁵ are identical or different and represent hydrogen; alkyl,alkenyl or alkinyl, each of which is optionally substituted; andoptionally substituted aralkyl,

R⁶ represents hydrogen, alkyl or alkylcarbonyl,

R⁷ represents optionally substituted alkyl, optionally substitutedalkenyl, optionally substituted alkinyl or optionally substituted benzyland

R⁸ represents hydrogen, optionally substituted alkyl, optionallysubstituted alkenyl, optionally substituted alkinyl or optionallysubstituted benzyl, or

R⁷ and R⁸ together represent divalent alkanediyl, it being possible fora CH₂ group to be replaced by O, S or NR⁶, where R⁶ has the meaningsindicated above,

are very highly suitable for controlling undesired microorganisms.

Depending on the nature of the substituents, the compounds of theformula (I) can exist as geometric and/or optical isomers or isomermixtures of differing composition. The invention relates both to the useof the pure isomers and of the isomer mixtures.

Formula (I) provides a general definition of thedibromo-thiophene-carboxylic acid derivatives which can be usedaccording to the invention.

R preferably represents the groups --XR¹, --NR² R³, --NR⁴ OR⁵ and --NR⁴--N(R⁵)₂.

X preferably represents oxygen or sulphur.

R¹ preferably represents hydrogen,

or straight-chain or branched alkyl having 1 to 12 carbon atoms, whichcan be mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, carboxyl, nitro; alkoxy,alkylthio or alkoxycarbonyl, each of which is straight-chain orbranched, each having 1 to 6 carbon atoms in the individual alkylmoieties; and also the group --NR⁷ R⁸, or

represents straight-chain or branched alkenyl and alkinyl having 3 to 6carbon atoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or

cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, which is optionally substitutedby cyano, where the cycloalkyl moiety of the two radicals mentioned canbe mono- to pentasubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms which isoptionally mono- to trisubstituted, identically or differently, by alkylhaving 1 to 4 carbon atoms, and/or by phenyl, which for its part can bemono- to trisubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen and straight-chainor branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, which is optionally mono-to trisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atomsin the aryl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, which is optionally substituted by cyano, whereeach of the two radicals in the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms; cycloalkyl having 3 to 7carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio, eachof which is straight-chain or branched, each having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms; and/or by phenyl whichfor its part can be mono- to trisubstituted, identically or differently,by halogen and/or alkyl having 1 to 4 carbon atoms, or

5- or 6-membered hetaryl or 5- or 6-membered hetarylalkyl having 1 to 6carbon atoms in the straight-chain or branched alkyl moiety, which isoptionally substituted by cyano, where the hetaryl moiety in each casecontains 1 to 3 heteroatoms, such as oxygen, sulphur and/or nitrogen,and can be mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 6 carbon atoms, halogen,cyano and/or straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 identical or different halogen atoms.

R² and R³ are identical or different and preferably represent hydrogen,or straight-chain or branched alkyl having 1 to 12 carbon atoms, whichcan be mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, nitro, straight-chain orbranched alkoxy having 1 to 6 carbon atoms, straight-chain or branchedalkylthio having 1 to 6 carbon atoms and/or the group ##STR7## orstraight-chain or branched alkenyl or alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or

cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, which is optionally substitutedby cyano, where the cycloalkyl moiety of the two radicals mentioned canbe mono- to pentasubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, optionallymono- to trisubstituted, identically or differently, by alkyl having 1to 4 carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, optionally mono- totrisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

aralkoxy having 6 or 10 carbon atoms in the aryl moiety and 1 to 4carbon atoms in the straight-chain or branched alkoxy moiety, optionallysubstituted by cyano, where the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio, each of which is straight-chain orbranched each having 1 to 4 carbon atoms; cycloalkyl having 3 to 7carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio, eachof which is straight-chain or branched, each having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms; and/or by phenyl, whichfor its part can be mono- to trisubstituted, identically or differently,by halogen and/or alkyl having 1 to 4 carbon atoms.

R³ additionally preferably represents 5- or 6-membered hetaryl or 5- or6-membered hetarylalkyl having 1 to 6 carbon atoms in the straight-chainor branched alkyl moiety, optionally substituted by cyano, where thehetaryl moiety in each case contains 1 to 3 heteroatoms, such as oxygen,sulphur and/or nitrogen, and can be mono- to trisubstituted, identicallyor differently, by straight-chain or branched alkyl having 1 to 6 carbonatoms, halogen, cyano and/or straight-chain or branched halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms.

R² and R³ additionally together preferably represent divalent alkanediylhaving 2 to 6 CH₂ groups, where a CH₂ group is optionally replaced by O,S or NR⁶.

R⁴ and R⁵ are identical or different and preferably represent hydrogen,or straight-chain or branched alkyl having 1 to 12 carbon atoms, whichcan be mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, carboxyl, nitro; alkoxy,alkylthio or alkoxycarbonyl, each of which is straight-chain orbranched, each having 1 to 6 carbon atoms in the individual alkylmoieties; and also the group --NR⁷ R⁸, or

straight-chain or branched alkenyl and alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or

aralkyl having 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, optionallysubstituted by cyano, where the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms; cycloalkyl having 3 to 7carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio, eachof which is straight-chain or branched, each having 1 to 4 carbon atomsand 1 to 5 identical or difcanent halogen atoms; and/or by phenyl, whichfor its part can be mono- to trisubstituted, identically or differently,by halogen and/or alkyl having 1 to 4 carbon atoms.

R⁶ preferably represents hydrogen, and also alkyl and alkylcarbonyl,each of which is straight-chain or branched, each having 1 to 6 carbonatoms in the alkyl moiety.

R⁷ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, which can be mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, nitro,carboxyl; alkoxy and alkoxycarbonyl, each of which is straight-chain orbranched, each having 1 to 6 carbon atoms in the alkoxy moieties;alkylamino and dialkylamino having 1 to 6 carbon atoms in eachstraight-chain or branched alkyl moiety, or

straight-chain or branched alkenyl or alkinyl each having 3 to 6 carbonatoms, each of which is optionally substituted by 1 to 5 identical ordifferent halogen atoms, or

benzyl which in the phenyl moiety can be mono- to trisubstituted,identically or differently, by halogen, nitro, cyano, straight-chain orbranched alkyl having 1 to 6 carbon atoms, and also halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms.

R⁸ preferably represents hydrogen, or straight-chain or branched alkylhaving 1 to 6 carbon atoms, which can be mono- to pentasubstituted,identically or differently, by halogen, cyano, amino, hydroxyl,mercapto, nitro, carboxyl; alkoxy and alkoxycarbonyl, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms in thealkoxy moieties, alkylamino and dialkylamino having 1 to 6 carbon atomsin each straight-chain or branched alkyl moiety, or

straight-chain or branched alkenyl or alkinyl each having 3 to 6 carbonatoms, each of which is optionally substituted by 1 to 5 identical ordifferent halogen atoms, or

benzyl which in the phenyl moiety can be mono- to trisubstituted,identically or differently, by halogen, nitro, cyano, straight-chain orbranched alkyl having 1 to 6 carbon atoms, and also halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms.

R⁷ and R⁸ additionally together preferably represent divalent alkanediylhaving 4 to 6 CH₂ groups, it optionally being possible for a CH₂ groupto be replaced by O, S or NR⁶ and R⁶ having the meanings mentioned aspreferred above.

R particularly preferably represents the groups --XR¹, --NR² R³, --NR⁴OR⁵ and --NR⁴ --N(R⁵)₂.

X particularly preferably represents oxygen or sulphur.

R¹ particularly preferably represents hydrogen, or straight-chain orbranched alkyl having 1 to 8 carbon atoms, which can be mono- totetrasubstituted, identically or differently, by fluorine, chlorine,cyano, amino, hydroxyl, mercapto; alkoxy and alkylthio, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms; and alsothe group --NR⁷ R⁸, or

straight-chain or branched alkenyl or alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to trisubstituted, identicallyor differently, by fluorine, chlorine and/or bromine, or

cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the cycloalkyl moiety of the two radicals mentioned can bemono- to tetrasubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms, cyclohexyl or cyclopentyl, optionally substituted by methyl orethyl, and/or by phenyl which for its part can be mono- ordisubstituted, identically or differently, by methyl, ethyl, fluorine,chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1 to 3identical or different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms, cyclohexyl or cyclopentyl, optionally substituted by methyl orethyl, and/or by phenyl, which for its part can be mono- ordisubstituted, identically or differently, by methyl, ethyl, fluorine,chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1 to 3identical or different halogen atoms, or

phenyl, naphthyl, phenylalkyl or naphthylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, optionallysubstituted by cyano, where each of the four radicals mentioned can bemono- to trisubstituted in the aryl moiety, identically or differently,by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms;cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms; and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 to 2 carbonatoms, or

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, fluorine, chlorine, bromine,cyano and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identicalor different halogen atoms.

R² and R³ are identical or different and particularly preferablyrepresent hydrogen, or straight-chain or branched alkyl having 1 to 8carbon atoms, which can be mono- to tetrasubstituted, identically ordifferently, by fluorine, chlorine, cyano, amino, hydroxyl, mercapto;alkoxy and alkylthio, each of which is straight-chain or branched, eachhaving 1 to 6 carbon atoms; and the group --NR⁷ R⁸, or cycloalkyl having3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7 carbon atoms in thecycloalkyl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, optionally substituted by cyano, where thecycloalkyl moiety of the two radicals mentioned can be mono- totetrasubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms, cyclohexyl or cyclopentyl, optionally substituted by methyl orethyl, and/or by phenyl, which for its part can be mono- ordisubstituted, identically or differently, by methyl, ethyl, fluorine,chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1 to 3identical or different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms, cyclohexyl or cyclopentyl, optionally substituted by methyl orethyl, and/or by phenyl, which for its part can be mono- ordisubstituted, identically or differently, by methyl, ethyl, fluorine,chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1 to 3identical or different halogen atoms, or

phenylalkoxy or naphthylalkoxy having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of these radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byhalogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms;cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 to 2 carbonatoms.

R³ additionally particularly preferably represents 5- or 6-memberedhetaryl or 5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms inthe straight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, fluorine, chlorine, bromine,cyano and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identicalor different halogen atoms.

R² and R³ additionally together particularly preferably representdivalent alkanediyl having 4 to 6 CH₂ groups, it optionally beingpossible for a CH₂ group to be replaced by O, S or NR⁶.

R⁴ and R⁵ are identical or different and particularly preferablyrepresent hydrogen, or straight-chain or branched alkyl having 1 to 8carbon atoms, which can be mono- to tetrasubstituted, identically ordifferently, by fluorine, chlorine, cyano, amino, hydroxyl, mercapto;alkoxy and alkylthio, each of which is straight-chain or branched, eachhaving 1 to 6 carbon atoms; and the group --NR⁷ R⁸, straight-chain orbranched alkenyl or alkinyl having 3 to 6 carbon atoms, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine, chlorine and/or bromine, or

phenylalkyl or naphthylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of the four radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byhalogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms;cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms; and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 to 2 carbonatoms.

R⁶ particularly preferably represents hydrogen, and also alkyl andalkylcarbonyl, each of which is straight-chain or branched, each having1 to 4 carbon atoms in the alkyl moiety.

R⁷ particularly preferably represents straight-chain or branched alkylhaving 1 to 6 carbon atoms, which can be mono- to tetrasubstituted,identically or differently, by fluorine, chlorine, cyano, amino,hydroxyl, carboxyl; and also alkoxy and alkoxycarbonyl, each of which isstraight-chain or branched, each having 1 to 4 carbon atoms in thealkoxy moieties; or

straight-chain or branched alkenyl having 3 to 6 carbon atoms,optionally substituted by 1 to 3 halogen atoms, straight-chain orbranched alkinyl having 3 to 6 carbon atoms, or

benzyl which can be mono- to trisubstituted in the phenyl moiety,identically or differently, by fluorine, chlorine and/or straight-chainor branched alkyl having 1 to 4 carbon atoms.

R⁸ particularly preferably represents hydrogen, or

straight-chain or branched alkyl having 1 to 6 carbon atoms, which canbe mono- to tetrasubstituted, identically or differently, by fluorine,chlorine, cyano, amino, hydroxyl, carboxyl; and also alkoxy andalkoxycarbonyl, each of which is straight-chain or branched, each having1 to 4 carbon atoms in the alkoxy moieties, or

straight-chain or branched alkenyl having 3 to 6 carbon atoms,optionally substituted by 1 to 3 halogen atoms,

straight-chain or branched alkinyl having 3 to 6 carbon atoms, or

benzyl which can be mono- to trisubstituted in the phenyl moiety,identically or differently, by fluorine, chlorine and/or straight-chainor branched alkyl having 1 to 4 carbon atoms.

R⁷ and R⁸ additionally together particularly preferably representdivalent alkanediyl having 4 to 6 CH₂ groups, it optionally beingpossible for a CH₂ group to be replaced by O, S or NR⁶ and R⁶ having themeanings mentioned above as particularly preferred.

R very particularly preferably represents the groups --XR¹, --NR² R³,--NR⁴ OR⁵ and --NR⁴ --N(R⁵)₂.

X very particularly preferably represents oxygen or sulphur.

R¹ very particularly preferably represents hydrogen, or

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n-or i-hexyl, n- or i-heptyl and n- or i-octyl, where each of theseradicals can be mono- to trisubstituted, identically or differently, byfluorine, chlorine, cyano, amino, hydroxyl, mercapto, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio or the group --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n-or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclopropyl-1-cyanoeth-1-yl,cyclopropyl-cyanomethyl,cyclopentyl,cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl,cyclopentyl-cyanomethyl, cyclopentyl-1-cyanoeth-1-yl, cyclohexyl,cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl,cyclohexyl-cyanomethyl, cyclohexyl-1-cyanoeth-1-yl, cycloheptyl,cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl,cycloheptyl-cyanomethyl or cycloheptyl-1-cyanoeth-1-yl, each of which isoptionally mono- to tetrasubstituted in the cycloalkyl moiety,identically or differently, by methyl, ethyl, n- or i-propyl, fluorine,chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or phenyl, naphthyl, phenylalkyl ornaphthylalkyl having 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, optionally substituted by cyano, where each ofthese radicals can be mono- to trisubstituted in the aryl moiety,identically or differently, by fluorine, chlorine, bromine, hydroxyl,cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl,trifluoromethyl, trifluoromethoxy, trifluoromethylthio or phenyl whichis optionally mono- to trisubstituted, identically or differently, byfluorine, chlorine, bromine, methyl and/or ethyl, or

5- or 6-membered hetaryl, or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, fluorine, chlorine, bromine, cyano,trifluoromethyl, difluoromethyl, chlorodifluoromethyl,bromodifluoromethyl, chloromethyl or dichloromethyl.

R² and R³ are identical or different and very particularly preferablyrepresent hydrogen, or

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n-or i-hexyl, n- or i-heptyl and n- or i-octyl, where each of theseradicals can be mono- to trisubstituted, identically or differently, byfluorine, chlorine, cyano, amino, hydroxyl, mercapto, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio or the group --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n-or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclopropyl-1-cyanoeth-1-yl, cyclopropyl-cyanomethyl, cyclopentyl,cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl,cyclopentyl-cyanomethyl, cyclopentyl-1-cyanoeth-1-yl, cyclohexyl,cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl,cyclohexyl-cyanomethyl, cyclohexyl-1-cyanoeth-1-yl, cycloheptyl,cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl,cycloheptyl-cyanomethyl or cycloheptyl-1-cyanoeth-1-yl, each of which isoptionally mono- to tetrasubstituted in the cycloalkyl moiety,identically or differently, by methyl, ethyl, n- or i-propyl, fluorine,chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or phenylalkoxy or naphthylalkoxy having 1 to4 carbon atoms in the straight-chain or branched, optionally lacuna! byfluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, cyclopropyl, cyclopentyl,cyclohexyl, cycloheptyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio or phenyl which is optionally mono- totrisubstituted, identically or differently, by fluorine, chlorine,bromine, methyl and/or ethyl.

R³ additionally very particularly preferably represents 5- or 6-memberedhetaryl, or 5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms inthe straight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, fluorine, chlorine, bromine, cyano,trifluoromethyl, difluoromethyl, chlorodifluoromethyl,bromodifluoromethyl, chloromethyl or dichloromethyl.

R² and R³ additionally together very particularly preferably representdivalent alkanediyl having 4 or 5 CH₂ groups, it optionally beingpossible for a CH₂ group to be replaced by O, S or NR⁶.

R⁴ and R⁵ are identical or different and very particularly preferablyrepresent hydrogen, or

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n-or i-hexyl, n- or i-heptyl and n- or i-octyl, where each of theseradicals can be mono- to trisubstituted, identically or differently, byfluorine, chlorine, cyano, amino, hydroxyl, mercapto, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio or the group --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n-or i-butinyl, n- or pentinyl and n- or i-hexinyl, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

phenylalkyl or naphthylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of the two radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byfluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, cyclopropyl, cyclopentyl,cyclohexyl, cycloheptyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio or phenyl which is optionally mono- totrisubstituted, identically or differently, by fluorine, chlorine,bromine, methyl and/or ethyl.

R⁶ very particularly preferably represents hydrogen, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, acetyl, ethylcarbonyl, n- ori-propylcarbonyl or n-, i-, s- or t-butylcarbonyl.

R⁷ very particularly preferably represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n- or i-pentyl and n- or i-hexyl, whereeach of these radicals can be mono- to trisubstituted, identically ordifferently, by cyano, amino, hydroxyl, carboxyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, acetyl, ethylcarbonyl, n- ori-propylcarbonyl and n-, i-, s- or t-butylcarbonyl, or

allyl, n- or i-butenyl, n- or i-pentenyl and n- or i-hexenyl, each ofwhich is optionally mono- to trisubstituted, identically or differently,by fluorine and/or chlorine, or

propargyl, n- or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, orbenzyl which can be mono- to trisubstituted in the phenyl moiety,identically or differently, by fluorine, chlorine, bromine, methyl,ethyl, n- or i-propyl and n-, i-, s- or t-butyl.

R⁸ very particularly preferably represents hydrogen, or

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl andn- or i-hexyl, where each of these radicals can be mono- totrisubstituted, identically or differently, by cyano, amino, hydroxyl,carboxyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,acetyl, ethylcarbonyl, n- or i-propylcarbonyl and n-, i-, s- ort-butylcarbonyl, or

allyl, n- or i-butenyl, n- or i-pentenyl and n- or i-hexenyl, each ofwhich is optionally mono- to trisubstituted, identically or differently,by fluorine and/or chlorine, or

propargyl, n- or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, orbenzyl which can be mono- to trisubstituted in the phenyl moiety,identically or differently, by fluorine, chlorine, bromine, methyl,ethyl, n- or i-propyl and n-, i-, s- or t-butyl.

R⁷ and R⁸ additionally very particularly preferably represent divalentalkanediyl having 4 or 5 CH₂ groups, it optionally being possible for aCH₂ group to be replaced by O, S or NR⁶ and R⁶ having the meaningsmentioned above as very particularly preferred.

The dibromo-thiophene-carboxylic acid derivatives of the formula (I)which can be used according to the invention are known in some cases(cf. Chem. Ber. 18(1885), 2312; DE-OS German Published Specification! 3901 074; U.S. Pat. No. 3,536,473 EP 0 258 790 JP-OS Japanese PublishedSpecification! 62-138, 489 and J. Chem. Soc. Perkin Trans. 1 (1973)1766, 1772, 1773).

New dibromo-thiophene-carboxylic acid derivatives are those of theformula ##STR8## in which R⁹ represents the groups --SR¹, --OR¹⁰,##STR9## R¹ represents hydrogen or straight-chain or branched alkylwhich can be substituted by halogen, cyano, amino, hydroxyl, mercapto,carboxyl, nitro, alkoxy, alkylthio, alkoxycarbonyl and/or the group##STR10## or R¹ represents optionally substituted alkenyl or optionallysubstituted alkinyl, or

R¹ represents cycloalkyl or cycloalkylalkyl, each of which is optionallysubstituted, tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, each of which is optionally substituted, or aryl,aralkyl, hetaryl or hetarylalkyl, each of which is optionallysubstituted,

R¹⁰ represents straight-chain or branched alkyl which is substituted byhalogen, cyano, amino, hydroxyl, mercapto, carboxyl, nitro, alkoxy,alkylthio, alkoxycarbonyl and/or the group ##STR11## or R¹⁰ representsoptionally substituted alkenyl or substituted alkinyl, or

R¹⁰ represents cycloalkyl or cycloalkylalkyl, each of which isoptionally substituted, tetrahydrofuran, tetrahydrothiophene,tetrahydropyran or tetrahydrothiopyran, each of which is optionallysubstituted, or

aryl, aralkyl, hetaryl or hetarylalkyl, each of which is optionallysubstituted,

R¹¹ and R¹² are identical or different and represent alkyl which issubstituted by halogen, cyano, amino, hydroxyl, mercapto, nitro, alkoxy,alkylthio and/or the group ##STR12## or alkenyl which is optionallysubstituted by halogen or alkinyl which is optionally substituted byhalogen, or

cycloalkyl or cycloalkylalkyl, where each of these radicals can besubstituted by alkyl, halogen, halogenoalkyl, cyano, alkylenedioxo,cycloalkyl which is optionally substituted by alkyl, and/or byoptionally substituted phenyl, or tetrahydrofuran, tetrahydrothiophene,tetrahydropyran or tetrahydrothiopyran, each of which is optionallysubstituted, or

optionally substituted aralkoxy,

R¹² additionally represents hetaryl or hetarylalkyl, each of which isoptionally substituted,

R¹¹ and R¹² furthermore together represent divalent alkanediyl, where aCH₂ group can be replaced by O, S or NR⁶,

R⁴ and R⁵ are identical or different and represent hydrogen; alkyl,alkenyl or alkinyl, each of which is optionally substituted; oroptionally substituted aralkyl,

R⁶ represents hydrogen, alkyl or alkylcarbonyl,

R⁷ represents optionally substituted alkyl, optionally substitutedalkenyl, optionally substituted alkinyl or optionally substituted benzyland

R⁸ represents hydrogen, optionally substituted alkyl, optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted alkinyl or optionally substituted benzyl, or

R⁷ and R⁸ together represent divalent alkanediyl, it being possible fora CH₂ group to be replaced by O, S or NR⁶, where R⁶ has the meaningsindicated above and

R¹³ represents hydrogen, substituted alkyl, optionally substitutedalkenyl, optionally substituted alkinyl or optionally substitutedaralkyl.

Dibromo-thiophene-carboxylic acid derivatives of the formula (I-A) canbe prepared by reacting dibromo-thiophene-carbonyl halides of theformula ##STR13## in which Hal represents halogen, either

a) with amines of the formula

    H--R.sup.14,                                               (III)

in which

R¹⁴ represents the groups ##STR14## in which R⁴, R⁵, R¹¹, R¹² and R¹³have the meanings indicated above, if appropriate in the presence of adiluent and if appropriate in the presence of a reaction auxiliary, or

b) with alcohols or thioalcohols of the formulae

    HO--R.sup.10                                               (IV)

or

    HS--R.sup.1,                                               (VI)

in which

R¹ and R¹⁰ have the meaning indicated above, if appropriate in thepresence of a diluent and if appropriate in the presence of a reactionauxiliary, and if appropriate in the presence of a catalyst.

The already-known dibromo-thiophene-carboxylic acid derivatives of theformula (I) can be prepared analogously.

Formula (I-A) provides a general definition of the newdibromo-thiophene-carboxylic acid derivatives.

R⁹ preferably represents the groups --SR¹, --OR¹⁰, ##STR15##

In connection with the definitions of the substituents of the formula(I-A), R¹, R⁴, R⁵, R⁶, R⁷ and R⁸ preferably represent those meaningswhich have already been mentioned above as preferred.

R¹⁰ preferably represents straight-chain or branched alkyl, having 1 to12 carbon atoms, which can be mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, carboxyl,nitro; alkoxy, alkylthio or alkoxycarbonyl, each of which isstraight-chain or branched, in each case having 1 to 6 carbon atoms inthe individual alkyl moieties; and also the group --NR⁷ R⁸, or

straight-chain or branched alkenyl and alkinyl, each having 3 to 6carbon atoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or cycloalkyl having 3 to 7carbon atoms or cycloalkylalkyl having 3 to 7 carbon atoms in thecycloalkyl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety which is optionally substituted by cyano, wherethe cycloalkyl moiety of the two radicals mentioned can be mono- topentasubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms which is optionally mono-to trisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms which is optionally mono-to trisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atomsin the aryl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, which is optionally substituted by cyano, whereeach of the two radicals in the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms; cycloalkyl having 3 to 7carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio, eachof which is straight-chain or branched, each having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms, and/or by phenyl whichfor its part can be mono- to trisubstituted, identically or differently,by halogen and/or alkyl having 1 to 4 carbon atoms, or

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 6 carbon atoms in thestraight-chain or branched alkyl moiety, which is optionally substitutedby cyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 6 carbon atoms, halogen, cyano and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms.

R¹¹ and R¹² are identical or different and preferably representstraight-chain or branched alkyl having 1 to 12 carbon atoms, which canbe mono- to pentasubstituted, identically or differently, by halogen,cyano, amino, hydroxyl, mercapto, nitro, straight-chain or branchedalkoxy having 1 to 6 carbon atoms, straight-chain or branched alkylthiohaving 1 to 6 carbon atoms and/or the group ##STR16## or straight-chainor branched alkenyl or alkinyl having 3 to 6 carbon atoms, each of whichis optionally mono- to pentasubstituted, identically or differently, byhalogen, or

cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, which is optionally substitutedby cyano, where the cycloalkyl moiety of the two radicals mentioned canbe mono- to pentasubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, optionallymono- to trisubstituted, identically or differently, by alkyl having 1to 4 carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, optionally mono- totrisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or

aralkoxy having 6 or 10 carbon atoms in the aryl moiety and 1 to 4carbon atoms in the straight-chain or branched alkoxy moiety, optionallysubstituted by cyano, where the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio in each case having 1 to 4 carbonatoms, each of which is straight-chain or branched; cycloalkyl having 3to 7 carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio,each of which is straight-chain or branched, each having 1 to 4 carbonatoms and 1 to 5 identical or different halogen atoms, and/or by phenyl,which for its part can be mono- to trisubstituted, identically ordifferently, by halogen and/or alkyl having 1 to 4 carbon atoms.

R¹² additionally preferably represents

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 6 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 6 carbon atoms, halogen, cyano and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms.

R¹¹ and R¹² additionally together preferably represent divalentalkanediyl having 2 to 6 CH₂ groups, where a CH₂ group is optionallyreplaced by O, S or NR⁶.

R¹³ preferably represents hydrogen, or straight-chain or branched alkylhaving 1 to 12 carbon atoms, which is mono- to pentasubstituted,identically or differently, by halogen, cyano, amino, hydroxyl,mercapto, carboxyl, nitro; alkoxy, alkylthio or alkoxycarbonyl, each ofwhich is straight-chain or branched, each having 1 to 6 carbon atoms inthe individual alkyl moieties; and also the group --NR⁷ R⁸, or

straight-chain or branched alkenyl and alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or

aralkyl having 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, optionallysubstituted by cyano, where the aryl moiety can be mono- totrisubstituted, identically or differently, by halogen, hydroxyl, cyano,nitro; alkyl, alkoxy or alkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms; cycloalkyl having 3 to 7carbon atoms; halogenoalkyl, halogenoalkoxy or halogenoalkylthio, eachof which is straight-chain or branched, each having 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms; and/or by phenyl, whichfor its part can be mono- to trisubstituted, identically or differently,by halogen and/or alkyl having 1 to 4 carbon atoms.

R⁹ particularly preferably represents the groups --SR¹, --OR¹⁰,##STR17##

In connection with the definitions of the substituents of the formula(I-A), R¹, R⁴, R⁵, R⁶, R⁷ and R⁸ particularly preferably represent thosemeanings which have already been mentioned above as particularlypreferred.

R¹⁰ particularly preferably represents straight-chain or branched alkylhaving 1 to 8 carbon atoms, which can be mono- to tetrasubstituted,identically or differently, by fluorine, chlorine, cyano, amino,hydroxyl, mercapto, alkoxy and alkylthio, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms, and thegroup --NR⁷ R⁸, or

straight-chain or branched alkenyl having 3 to 6 carbon atoms,optionally mono- to trisubstituted, identically or differently, byfluorine, chlorine and/or bromine, or

straight-chain or branched alkinyl having 3 to 6 carbon atoms, mono- totrisubstituted, identically or differently, by fluorine, chlorine and/orbromine, or cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkylhaving 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, optionallysubstituted by cyano, where the cycloalkyl moiety of the two radicalsmentioned can be mono- to tetrasubstituted, identically or differently,by straight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 3 identical or different halogen atoms, cyano, alkylenedioxo having1 or 2 carbon atoms; cyclohexyl or cyclopentyl, each of which isoptionally substituted by methyl or ethyl; and/or by phenyl which forits part can be mono- or disubstituted, identically or differently, bymethyl, ethyl, fluorine, chlorine and/or halogenoalkyl having 1 or 2carbon atoms and 1 to 3 identical or different halogen atoms, or

phenyl, naphthyl, phenylalkyl or naphthylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, optionallysubstituted by cyano, where each of the four radicals mentioned can bemono- to trisubstituted in the aryl moiety, identically or differently,by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms;cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms; and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 to 2 carbonatoms, or

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, fluorine, chlorine, bromine,cyano and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identicalor different halogen atoms.

R¹¹ and R¹² are identical or different and particularly preferablyrepresent straight-chain or branched alkyl having 1 to 8 carbon atoms,which can be mono- to tetrasubstituted, identically or differently, byfluorine, chlorine, cyano, amino, hydroxyl, mercapto; alkoxy andalkylthio, each of which is straight-chain or branched, each having 1 to6 carbon atoms; and the group --NR⁷ R⁸, or straight-chain or branchedalkenyl or alkinyl having 3 to 6 carbon atoms, in each case optionallymono- to trisubstituted, identically or differently, by fluorine,chlorine and/or bromine, or

cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the cycloalkyl moiety of the two radicals mentioned can bemono- to tetrasubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms; cyclohexyl or cyclopentyl, each of which is optionallysubstituted by methyl or ethyl; and/or by phenyl, which for its part canbe mono- or disubstituted, identically or differently, by methyl, ethyl,fluorine, chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1to 3 identical or different halogen atoms, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 identicalor different halogen atoms, cyano, alkylenedioxo having 1 or 2 carbonatoms; cyclohexyl or cyclopentyl, each of which is optionallysubstituted by methyl or ethyl; and/or by phenyl, which for its part canbe mono- or disubstituted, identically or differently, by methyl, ethyl,fluorine, chlorine and/or halogenoalkyl having 1 or 2 carbon atoms and 1to 3 identical or different halogen atoms, or

phenylalkoxy or naphthylalkoxy having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of these radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byhalogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms;cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 2 carbon atoms and 1 to 5 identical or different halogenatoms; and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 to 2 carbonatoms.

R¹² additionally particularly preferably represents

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, fluorine, chlorine, bromine,cyano and halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identicalor different halogen atoms.

R¹¹ and R¹² additionally together particularly preferably representdivalent alkanediyl having 4 to 6 CH₂ groups, it optionally beingpossible for a CH₂ group to be replaced by O, S or NR⁶.

R¹³ particularly preferably represents hydrogen, or straight-chain orbranched alkyl having 1 to 8 carbon atoms, which can be mono- totetrasubstituted, identically or differently, by fluorine, chlorine,cyano, amino, hydroxyl, mercapto; alkoxy and alkylthio, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms; and thegroup --NR⁷ R⁸, or

straight-chain or branched alkenyl or alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to trisubstituted, identicallyor differently, by fluorine, chlorine and/or bromine, or

phenylalkyl or naphthylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of the two radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byhalogen, hydroxyl, cyano, nitro; alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched, each having 1 to 4 carbon atoms,cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 or 2 carbon atoms and 1 to 5 identical or different halogenatoms; and/or phenyl which is optionally mono- to trisubstituted,identically or differently, by halogen and/or alkyl having 1 or 2 carbonatoms.

R⁹ very particularly preferably represents the groups --SR¹, --OR¹⁰,##STR18##

In connection with the definitions of the substituents of the formula(I-A), R¹, R⁴, R⁵, R⁶, R⁷ and R⁸ very particularly preferably representthose meanings which have already been mentioned above as veryparticularly preferred.

R¹⁰ very particularly preferably represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- ori-heptyl and n- or i-octyl, where each of these radicals can be mono- totrisubstituted, identically or differently, by fluorine, chlorine,cyano, amino, hydroxyl, mercapto, methoxy, ethoxy, n- or i-propoxy, n-,i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio or thegroup --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, each of whichis optionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

propargyl, n- or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, eachof which is optionally mono- to trisubstituted, identically ordifferently, by fluorine and/or chlorine, or

cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclopropyl-1-cyanoeth-1-yl,cyclopropyl-cyanomethyl,cyclopentyl,cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl,cyclopentyl-cyanomethyl, cyclopentyl-1-cyanoeth-1-yl, cyclohexyl,cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl,cyclohexyl-cyanomethyl, cyclohexyl-1-cyanoeth-1-yl, cycloheptyl,cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl,cycloheptyl-cyanomethyl or cycloheptyl-1-cyanoeth-1-yl, each of which isoptionally mono- to tetrasubstituted in the cycloalkyl moiety,identically or differently, by methyl, ethyl, n- or i-propyl, fluorine,chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, fluoro, chloro, bromo, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or phenyl, naphthyl, phenylalkyl ornaphthylalkyl having 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, optionally substituted by cyano, where each ofthese radicals can be mono- to trisubstituted in the aryl moiety,identically or differently, by fluorine, chlorine, bromine, hydroxyl,cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,ethylthio, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl,trifluoromethyl, trifluoromethoxy, trifluoromethylthio or phenyl whichis optionally mono- to trisubstituted, identically or differently, byfluorine, chlorine, bromine, methyl and/or ethyl, or

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, fluorine, chlorine, bromine, cyano,trifluoromethyl, difluoromethyl, chlorodifluoromethyl,bromodifluoromethyl, chloromethyl or dichloromethyl.

R¹¹ and R¹² are identical or different and very particularly preferablyrepresent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- ori-pentyl, n- or i-hexyl, n- or i-heptyl and n- or i-octyl, where each ofthese radicals is mono- to trisubstituted, identically or differently,by fluorine, chlorine, cyano, amino, hydroxyl, mercapto, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio or the group --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n-or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclopropyl-1-cyanoeth-1-yl, cyclopropyl-cyanomethyl, cyclopentyl,cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl,cyclopentyl-cyanomethyl, cyclopentyl-1-cyanoeth-1-yl, cyclohexyl,cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl,cyclohexyl-cyanomethyl, cyclohexyl-1-cyanoeth-1-yl, cycloheptyl,cycloheptylmethyl, cycloheptylethyl, cycloheptylpropyl,cycloheptyl-cyanomethyl or cycloheptyl-1-cyanoeth-1-yl, each of which isoptionally mono- to tetrasubstituted in the cycloalkyl moiety,identically or differently, by methyl, ethyl, n- or i-propyl, fluorine,chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or

tetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals can be mono- totrisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, bromodifluoromethyl, chloromethyl, dichloromethyl,cyano, methylenedioxo, ethylenedioxo, methylcyclopentyl,methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, phenyl,chlorophenyl, dichlorophenyl, fluorophenyl, difluorophenyl,chlorofluorophenyl, methylphenyl, dimethylphenyl, chloromethylphenyl,fluoromethylphenyl, trifluoromethylphenyl, chloro-trifluoromethylphenylor fluoro-trifluoromethyl, or phenylalkoxy or naphthylalkoxy having 1 to4 carbon atoms in the straight-chain or branched alkyl moiety,optionally substituted by cyano, where each of these radicals mentionedcan be mono- to trisubstituted in the aryl moiety, identically ordifferently, by fluorine, chlorine, bromine, hydroxyl, cyano, nitro,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio or phenyl which is optionallymono- to trisubstituted, identically or differently, by fluorine,chlorine, bromine, methyl and/or ethyl.

R¹² additionally very particularly preferably represents

5- or 6-membered hetaryl or

5- or 6-membered hetarylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where the hetaryl moiety in each case contains 1 to 3heteroatoms, such as oxygen, sulphur and/or nitrogen, and can be mono-to trisubstituted, identically or differently, by methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, fluorine, chlorine, bromine, cyano,trifluoromethyl, difluoromethyl, chlorodifluoromethyl,bromodifluoromethyl, chloromethyl or dichloromethyl.

R¹¹ and R¹² additionally together very particularly preferably representdivalent alkanediyl having 4 or 5 CH₂ groups, it optionally beingpossible for a CH₂ group to be replaced by O, S or NR⁶.

R¹³ very particularly preferably represents hydrogen, or

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n-or i-hexyl, n- or i-heptyl and n- or i-octyl, where each of theseradicals can be mono- to trisubstituted, identically or differently, byfluorine, chlorine, cyano, amino, hydroxyl, mercapto, methoxy, ethoxy,n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio or the group --NR⁷ R⁸, or

allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n-or i-butinyl, n- or i-pentinyl and n- or i-hexinyl, each of which isoptionally mono- to trisubstituted, identically or differently, byfluorine and/or chlorine, or

phenylalkyl or naphthylalkyl having 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, optionally substituted bycyano, where each of the two radicals mentioned can be mono- totrisubstituted in the aryl moiety, identically or differently, byfluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylthio, ethylthio, cyclopropyl, cyclopentyl,cyclohexyl, cycloheptyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio or phenyl which is optionally mono- totrisubstituted, identically or differently, by fluorine, chlorine,bromine, methyl and/or ethyl.

If, for example, 4,5-dibromo-thiophene-2-carbonyl chloride andbenzyloxyamine are used as starting substances, the course of thereaction of process (a) according to the invention can be represented bythe following equation: ##STR19##

If, for example, 4,5-dibromo-thiophene-2-carbonyl bromide andcyclohexanol are used as starting substances, the course of the reactionof process (b) according to the invention can be represented by thefollowing equation: ##STR20##

Formula (II) provides a general definition of thedibromo-thiophene-carbonyl halides needed as starting substances forcarrying out processes (a) and (b) according to the invention. In thisformula (II), Hal is preferably chlorine or bromine.

The dibromo-thiophene-carbonyl halides of the formula (II) are known(cf., for example, EP-OS European Published Specification! 0 450 355;U.S. Pat. No. 3,303,201; DE-OS German Published Specification) 12 01952; GB-PS 1085 974).

Formula (III) provides a general definition of the amines furthermoreneeded as starting substances for carrying out process (a) according tothe invention. In this formula (III), R¹⁴ preferably represents thegroups --NR¹¹ R¹², --NR⁴ OR¹³ and --NR⁴ --N(R⁵)₂, where R⁴, R⁵, R¹¹, R¹²and R¹³ preferably represent those radicals which have already beenmentioned as preferred for these substituents in connection with thedescription of the compounds of the formulae (I) and (I-A) which can beused according to the invention.

The amines of the formula (III) are generally known compounds of organicchemistry or are obtainable in analogy to generally known processes.

Formulae (IV) and (V) provide a general definition of the alcohols andthioalcohols furthermore needed as starting substances for carrying outprocess (b) according to the invention. In these formulae (IV) and (V),R¹ and R¹⁰ preferably represent those radicals which have already beenmentioned as preferred for these substituents in connection with thedescription of the compounds of the formulae (I) and (I-A) which can beused according to the invention.

The alcohols of the formula (IV) and the thioalcohols of the formula (V)are generally known compounds of organic chemistry or are obtainable inanalogy to generally known processes.

Possible diluents for carrying out process (a) according to theinvention are inert organic solvents. Those which can preferably be usedare aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons, such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, carbon tetrachloride; ethers, such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethyleneglycol dimethyl or diethyl ether; ketones, such as acetone, butanone ormethyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoramide; esters such as methyl acetate or ethyl acetateor sulphoxides, such as dimethyl sulphoxide.

Process (a) according to the invention is preferably carried out in thepresence of a suitable reaction auxiliary. Those which are suitable areall customary inorganic or organic bases. Those which can preferably beused are alkaline earth metal or alkali metal hydrides, hydroxides,amides, alkoxides, acetates, carbonates or hydrogen carbonates, such as,for example, sodium hydride, sodium amide, sodium methoxide, sodiumethoxide, potassium tert-butoxide, sodium hydroxide, potassiumhydroxide, sodium acetate, potassium acetate, calcium acetate, sodiumcarbonate, potassium carbonate, potassium hydrogen carbonate, sodiumhydrogen carbonate, and further ammonium hydroxide, ammonium acetate orammonium carbonate as well as tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Process (a) according to the invention can optionally also be carriedout in a two-phase system, such as, for example, water/toluene orwater/dichloromethane, if appropriate in the presence of a suitablephase-transfer catalyst. Examples of such catalysts which may bementioned are: tetrabutylammonium iodide, tetrabutylammonium bromide,tetrabutylammonium chloride, tributyl-methylphosphonium bromide,trimethyl-C₁₃ /C₁₅ -alkylammonium chloride, trimethyl-C₁₃ /C₁₅-alkylammonium bromide, dibenzyldimethyl-ammonium methylsulphate,dimethyl-C₁₂ /C₁₄ -alkyl-benzylammonium chloride, dimethyl-C₁₂ /C₁₄-alkyl-benzyl-ammonium bromide, tetrabutylammonium hydroxide,triethylbenzylammonium chloride, methyltrioctylammonium chloride,trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris-2-(2-methoxyethoxy)-ethyl!-amine.

When carrying out process (a) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between -20° C. and 150° C.,preferably at temperatures between 0° C. and 120° C.

Process (a) according to the invention is customarily carried out undernormal pressure. However, it is also possible to work at elevated orreduced pressure.

To carry out process (a) according to the invention, in general 1.0 to5.0 mol, preferably 1.0 to 2.5 mol, of amine of the formula (III) andoptionally 1.0 to 5.0 mol. preferably 1.0 to 2.5 mol, of base used asreaction auxiliary are employed per mole of dibromo-thiophene-carbonylhalide of the formula (II). The reaction is carried out and worked upand the reaction products are isolated according to generally knownprocesses (cf. for this also the Preparation Examples).

Suitable diluents for carrying out process (b) according to theinvention are inert organic solvents. Those which can preferably be usedare aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons, such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, carbon tetrachloride; ethers, such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethyleneglycol dimethyl or diethyl ether; nitriles, such as acetonitrile,propionitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoramide or sulphoxides, such as dimethyl sulphoxide.

Process (b) according to the invention is preferably carried out in thepresence of a suitable reaction auxiliary. Those which are suitable areall customary inorganic or organic bases. Those which can preferably beused are alkaline earth metal or alkali metal hydrides, hydroxides,amides, alkoxides, acetates, carbonates or hydrogen carbonates, such as,for example, sodium hydride, sodium amide, sodium methoxide, sodiumethoxide, potassium tert-butoxide, sodium hydroxide, potassiumhydroxide, sodium acetate, potassium acetate, calcium acetate, sodiumcarbonate, potassium carbonate, potassium hydrogen carbonate, sodiumhydrogen carbonate, and further ammonium hydroxide, ammonium acetate orammonium carbonate as well as tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline, pyridine,N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Process (b) according to the invention is additionally optionallycarried out in the presence of a suitable catalyst. Those which aresuitable are in particular copper(I) salts, such as, for example,copper(I) chloride. In this connection, the addition of catalyticamounts of a suitable phase-transfer catalyst, such as, for example,15-crown-5, 18-crown-6 or tris- 2-(2-methoxyethoxy)-ethyl!-amine, can beadvantageous.

When carrying out process (b) according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between -20° C. and +180°C., preferably at temperatures between 0° C. and +150° C.

Process (b) according to the invention is customarily carried out undernormal pressure. However, it is also possible to work at elevated orreduced pressure.

To carry out process (b) according to the invention, in general 1.0 to3.0 mol, preferably 1.0 to 1.5 mol, of alcohol of the formula (IV) orthioalcohol of the formula (V) and optionally 0.1 to 3.0 mol, preferably0.5 to 1.5 mol, of base used as reaction auxiliary are employed per moleof dibromo-thiophene-carbonyl halide of the formula (II). The reactionis carried out and worked up, and the reaction products are in each caseisolated according to generally known processes (cf. for this also thePreparation Examples).

Purification of the final products of the formula (I) is carried outwith the aid of customary processes, for example by columnchromatography or by recrystallization.

Characterization is carried out with the aid of the melting point or, inthe case of non-crystallizing compounds, with the aid of the refractiveindex or of proton nuclear magnetic resonance spectroscopy (¹ H-NMR).

The active compounds of the formula (I), according to the invention,have a potent action against microorganisms and can be employed inpractice for controlling undesired microorganisms. The active compoundsare particularly suitable for use as fungicides and resistance inducers.

Fungicidal agents in plant protection are employed for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Some causative organisms of fungal diseases which come under the genericnames listed above may be mentioned as examples, but not by way oflimitation:

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Pseudoperonospora humuli orPseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechlera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellucularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

The active compounds according to the invention can be employed here toparticularly good effect for controlling diseases in fruit- andvegetable-growing, such as, for example, against the causative organismof late blight of tomato (Phytophthora infestans) or against thecausative organism of apple scab (Venturia inaequalis) or against thecausative organism of powdery mildew on grapevines (Uncinula necator) oragainst the causative organism of rust on beans (Uromycesappendiculatus) or for controlling rice diseases, such as, for example,against the causative organism of rice blast disease (Pyriculariaoryzae) or for controlling powdery mildew fungi on cereals, apples andcucumbers and also for controlling Alternaria solani and Peronosporabrassicae.

The active compounds according to the invention additionally have astrong resistance-inducing action in plants. They are therefore suitablefor producing resistance in plants to attack by undesiredmicroorganisms.

Resistant-inducing substances are understood in the present context asmeaning those substances which on the one hand, when acting directly onthe undesired microorganisms, only exhibit a low activity, but are ableto stimulate the defence system of plants such that the treated plants,when subsequently inoculated with undesired microorganisms, displayextensive resistance to these microorganisms.

Undesired microorganisms are to be understood in the present case asmeaning phytophatogenic fungi, bacteria and viruses. The substancesaccording to the invention can thus be employed in order to produceresistance in plants within a certain period of time after treatment toattack by the harmful causative organisms mentioned. The period of timewithin which resistance is produced in general extends from 1 to 10days, preferably 1 to 7 days, after the treatment of the plants with theactive compounds.

The undesired microorganisms in plant protection include fungi from theclasses of the Plasmodiophoromycetes, Oomycetes, Chytridiomycetes,Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted to the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, as well as ULV cold mist and warm mistformulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents. In the case of the use of water as an extender,organic solvents can, for example, also be used as auxiliary solvents.As liquid solvents, there are suitable in the main: aromatics, such asxylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-disperse silica, alumina and silicates; assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospho-lipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in theirformulations can also be used as a mixture with known fingicides,bactericides, acaricides, nematicides or insecticides, for example towiden the spectrum of action or to prevent the build-up of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of particularly advantageous mixtures are the followingcompounds.

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide;8-hydroxyquinoline sulphate; methyl (E)-2-{2-6-(2-cyanophenoxy)pyrimidin-4-yloxy!-phenyl}-3-methoxyacrylate; methyl(E)-methoximino alpha-(o -tolyloxy)-o-tolyl!-acetate; 2-phenylphenol(OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon, edifenphos, epoxyconazole,

ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane,

kasugamycin, copper preparations such as: copper hydroxide, coppernaphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb,mepanipyrim, mepronil, metalaxyl, metconazole,

methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin,polyoxin, probenazole, prochloraz, procymidone, proparnocarb,propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,pyroquilon,

quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram

Bactericides

bromopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations

Insecticides/Acaricides/Nematicides

abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb,aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,azinphos A, azinphos M, azocyclotin,

Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,beta-cyluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucytirinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivemectin,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, pirimiphos A,profenophos, promecarb, propaphos, propoxur, prothiophos, prothoate,pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, zetamethrin.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators is also possible.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering, dusting, foaming, brushing onand the like.

It is furthermore possible to apply the active compounds by theultra-low volume method or to inject the active compound formulation orthe active compound itself into the soil. The seeds of the plants canalso be treated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02% by weight, are required atthe place of action.

When used as resistance inducers, the active compound concentrations forthe treatment of parts of plants can be varied within a relatively widerange in the use forms. In general, they are between 1 and 0.0001% byweight, preferably between 0.5 and 0.001% by weight.

The preparation and the use of the substances according to the inventionis illustrated by the following examples.

PREPARATION EXAMPLES Example 1 ##STR21## (Process a)

10 g (0.034 mol) of 4,5-dibromo-thiophene-2-carbonyl chloride in 100 mlof toluene are treated dropwise at room temperature with 5.0 g (0.068mol) of tert-butyl-amine in 20 ml of toluene. The reaction mixture isthen stirred at 50° C. for one hour, cooled to room temperature andtreated with water. The organic phase is separated off, rewashed withwater and concentrated under reduced pressure. After treating theresidue with hexane, the crystalline residue which is deposited isfiltered off and dried at 50° C. under reduced pressure. 4.8 g (41.4% oftheory) of 4,5-dibromo-thiophene-2-carboxylic acid t-butyl-amide ofmelting point 190° C. are obtained.

Example 2 ##STR22## (Process b)

5 g (0.014 mol) of 4,5-dibromo-thiophene-2-carbonyl bromide in 40 ml ofchloroform are treated with 1.5 g (0.015 mol) of cyclohexanol. Thisreaction mixture is treated dropwise with 2.1 g (0.021 mol) oftriethylamine in 5 ml of chloroform and then stirred at room temperaturefor 2 hours.

It is then treated with water, and the organic phase is separated off,washed with water and concentrated under reduced pressure. The residueis purified by column chromatography (silica gel/methylene chloride).4.23 g (81.1% of theory) of cyclohexyl4,5-dibromo-thiophene-2-carboxylate of refractive index n_(D) ²⁰ =1.5845are obtained.

The following dibromo-thiophene-carboxylic acid derivatives of theformula (I) are obtained correspondingly and according to the generaldetails for preparation:

                  TABLE 1                                                         ______________________________________                                         ##STR23##                                                                    Example                      Physical                                         No.     R                    constant                                         ______________________________________                                         3                                                                                     ##STR24##           m.p. 109° C.                               4      NHNH.sub.2           m.p. 192-194° C.                           5      OCH.sub.2 CH.sub.2 OCH.sub.3                                                                       m.p. 37° C.                                6      OH                   m.p. 222-224° C.                           7      NH.sub.2             m.p. 167-168° C.                           8      OCH.sub.3            m.p. 73-75° C.                             9      OC.sub.3 H.sub.7 -n  n.sub.D.sup.20 = 1.5759                          10      OC.sub.3 H.sub.7 -i  n.sub.D.sup.20 = 1.5764                          11                                                                                     ##STR25##           m.p. 70-72° C.                            12                                                                                     ##STR26##           m.p. 113-115° C.                          13      OCH.sub.2 CHCH.sub.2 n.sub.D.sup.20 = 1.5962                          14      OCH.sub.2 C CH       m.p. 54° C.                               15                                                                                     ##STR27##           n.sub.D.sup.20 = 1.5981                          16                                                                                     ##STR28##           m.p. 65° C.                               17      OC.sub.4 H.sub.9 -n  n.sub.D.sup.20 = 1.5599                          18      N(C.sub.2 H.sub.5).sub.2                                                                           n.sub.D.sup.20 = 1.6038                          19      OCH(CH.sub.3)C.sub.4 H.sub.9 -t                                                                    .sup.1 H-NMR (CDCl.sub.3)                                                     δ = 0.96 ppm (3H)                          20      OCH.sub.2 C.sub.3 H.sub.7 -i                                                                       n.sub.D.sup.20 = 1.5599                          21      OCH(CH.sub.3)C CH    m.p. 38° C.                               22      OCH(CH.sub.3)CHCH.sub.2                                                                            n.sub.D.sup.20 = 1.5819                          23      OCH.sub.2 CH.sub.2 C(CH.sub.3)CH.sub.2                                                             n.sub.D.sup.20 = 1.5749                          24                                                                                     ##STR29##           m.p. 236-237° C.                          25                                                                                     ##STR30##           m.p. 168-169° C.                          26                                                                                     ##STR31##           m.p. 143-145° C.                          27                                                                                     ##STR32##           m.p. 168-169° C.                          28                                                                                     ##STR33##           m.p. 247-249° C.                          29                                                                                     ##STR34##           m.p. 164-165° C.                          30                                                                                     ##STR35##           m.p. 249-250° C.                          31                                                                                     ##STR36##           m.p. 221-222° C.                          32                                                                                     ##STR37##           m.p. 283-284° C.                          33                                                                                     ##STR38##           m.p. 189-191° C.                          34                                                                                     ##STR39##           m.p. 202-208° C.                          35      OCH(CH.sub.3)C.sub.2 H.sub.5                                                                       n.sub.D.sup.20 = 1.5635                          36      NHCH(OH)CCl.sub.3    m.p. 175° C.                              37      NHCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 -i                                                   m.p. 80° C.                               38      NHCH.sub.2 CH.sub.2 OH                                                                             m.p. 120-122° C.                          39                                                                                     ##STR40##           m.p. 154-157° C.                          ______________________________________                                    

Use Examples Example A

Pyricularia test (rice)/protective

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents, and theconcentrate is diluted with water and the stated amount of emulsifier tothe desired concentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Pyricularia oryzae. The plants are then placed in agreenhouse at 100% relative atmospheric humidity and 25° C.

Evaluation of the disease infestation is carried out 4 days after theinoculation.

Active compounds, active compound concentrations and experimentalresults can be seen in the following table.

                                      TABLE A                                     __________________________________________________________________________    Pyricularia test (rice)/protective                                                                             Efficacy in % of                                                     Active compound                                                                        the untreated                                Active compound         concentration in %                                                                     control                                      __________________________________________________________________________    According to the invention                                                     ##STR41##              0.025    70                                            ##STR42##              0,025    80                                            ##STR43##              0.025    70                                            ##STR44##              0.025    80                                           __________________________________________________________________________

Example B

Uncinula test (grapevine)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are dusted with conidia of the fungusUnicinula necator.

The plants are then placed in a greenhouse at 23° to 24° C. and arelative atmospheric humidity of about 75%.

Evaluation is carried out 14 days after the inoculation.

Active compounds, active compound concentrations and experimentalresults can be seen in the following table.

                                      TABLE B                                     __________________________________________________________________________    Uncinula test (grapevine)/protective                                                                  Efficacy in % of the                                                          untreated control at an                                                       active compound                                       Active compound         concentration of 25 ppm.                              __________________________________________________________________________     ##STR45##              100                                                   __________________________________________________________________________

We claim:
 1. A dibromo-thiophene-carboxylic acid derivative of theformula (I-A): ##STR46## in which R⁹ represents the groups --OR¹⁰,##STR47## in which R¹⁰ represents straight-chain or branched alkylhaving 1 to 12 carbon atoms, which is mono- to pentasubstituted,identically or differently, by halogen or alkoxy having 1 to 6 carbonatoms; orrepresents straight-chain or branched alkenyl having 3 to 6carbon atoms; or represents cycloalkyl having 3 to 7 carbon atoms orcycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and1 to 4 carbon atoms in the straight-chain or branched alkyl moiety; orrepresents aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkyl moiety, which alkyl moiety isoptionally substituted by cyano, and wherein each of the aryl moietiesis optionally mono- to trisubstituted, identically or differently, byhalogen, hydroxyl, cyano, nitro, alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched and has 1 to 4 carbon atoms,cycloalkyl having 3 to 7 carbon atoms, halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, has 1 to4 carbon atoms, and 1 to 5 identical or different halogen atoms, orphenyl, which is optionally mono- to trisubstituted, identically ordifferently, by halogen or alkyl having 1 to 4 carbon atoms; R¹¹represents hydrogen or straight-chain or branched alkyl having 1 to 12carbon atoms; R¹² represents straight-chain or branched alkyl having 1to 12 carbon atoms, which is mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, nitro,straight-chain or branched alkoxy having 1 to 6 carbon atoms, orstraight-chain or branched alkylthio having 1 to 6 carbon atoms;orrepresents cycloalkyl having 3 to 7 carbon atoms or cycloalkylalkylhaving 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, which alkyl moietyis optionally substituted by cyano, and wherein each of the cycloalkylmoieties is optionally mono- to pentasubstituted, identically ordifferently, by straight-chain or branched alkyl having 1 to 4 carbonatoms, halogen, straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 identical or different halogen atoms, cyano,alkylenedioxo having 1 to 3 carbon atoms, or cycloalkyl having 3 to 7carbon atoms, which is optionally mono- to trisubstituted, identicallyor differently, by alkyl having 1 to 4 carbon atoms and/or by phenyl,which phenyl is optionally mono- to trisubstituted, identically ordifferently, by straight-chain or branched alkyl having 1 to 4 carbonatoms, halogen, or straight-chain or branched halogenoalkyl having 1 to4 carbon atoms and 1 to 5 identical or different halogen atoms; orrepresents tetrahydrothiophene or tetrahydropyran, each of which isoptionally mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, or cycloalkyl having 3 to 7 carbon atoms, which isoptionally mono- to trisubstituted, identically or differently, by alkylhaving 1 to 4 carbon atoms and/or by phenyl, which phenyl is optionallymono- to trisubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen, or straight-chainor branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms; or represents aralkoxy having 6 or10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in thestraight-chain or branched alkoxy moiety, which alkoxy moiety isoptionally substituted by cyano, and wherein the aryl moiety isoptionally mono- to trisubstituted, identically or differently, byhalogen, hydroxyl, cyano, nitro, alkyl, alkoxy or alkylthio, each ofwhich is straight-chain or branched and has 1 to 4 carbon atoms,cycloalkyl having 3 to 7 carbon atoms, halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, has 1 to4 carbon atoms, and 1 to 5 identical or different halogen atoms, orphenyl, which is optionally mono- to trisubstituted, identically ordifferently, by halogen or alkyl having 1 to 4 carbon atoms; R⁴ and R⁵are identical or different and represent straight-chain or branchedalkyl having 1 to 12 carbon atoms, which is mono- to pentasubstituted,identically or differently, by halogen, cyano, amino, hydroxyl,mercapto, carboxyl, nitro, alkoxy, alkylthio or alkoxycarbonyl, each ofwhich is straight-chain or branched and has 1 to 6 carbon atoms in theindividual alkyl moieties, --NR⁷ R⁸, or straight-chain or branchedalkenyl or alkynyl, each of which has 3 to 6 carbon atoms and isoptionally mono- to pentasubstituted by identical or different halogen;R⁷ represents straight-chain or branched alkyl having 1 to 6 carbonatoms, which is optionally mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, nitro,carboxyl, alkoxy or alkoxycarbonyl, each of which is straight-chain orbranched and has 1 to 6 carbon atoms in the alkoxy moieties, oralkylamino or dialkylamino, each of which has 1 to 6 carbon atoms ineach straight-chain or branched alkyl moiety; orrepresentsstraight-chain or branched alkenyl or alkynyl, each having 3 to 6 carbonatoms and being optionally substituted by 1 to 5 identical or differenthalogen atoms; or represents benzyl, which is optionally mono- totrisubstituted on the phenyl moiety, identically or differently, byhalogen, nitro, cyano, straight-chain or branched alkyl having 1 to 6carbon atoms, or halogenoalkyl, halogenoalkoxy, or halogenoalkylthio,each of which is straight-chain or branched, has 1 to 4 carbon atoms,and 1 to 5 identical or different halogen atoms; R⁸ represents hydrogen,or straight-chain or branched alkyl having 1 to 6 carbon atoms, which isoptionally mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, nitro, carboxyl, alkoxy oralkoxycarbonyl, each of which is straight-chain or branched and has 1 to6 carbon atoms in the alkoxy moieties, or alkylamino or dialkylamino,each of which has 1 to 6 carbon atoms in each straight-chain or branchedalkyl moiety; orrepresents straight-chain or branched alkenyl oralkynyl, each having 3 to 6 carbon atoms and being optionallysubstituted by 1 to 5 identical or different halogen atoms; orrepresents benzyl, which is optionally mono- to trisubstituted on thephenyl moiety, identically or differently, by halogen, nitro, cyano,straight-chain or branched alkyl having 1 to 6 carbon atoms, orhalogenoalkyl, halogenoalkoxy, or halogenoalkylthio, each of which isstraight-chain or branched, has 1 to 4 carbon atoms, and 1 to 5identical or different halogen atoms; or R⁷ and R⁸ together representdivalent alkanediyl having 4 to 6 methylene groups, it being possiblefor a methylene group to be replaced by O, S or NR⁶, wherein R⁶represents hydrogen, or alkyl or alkoxycarbonyl, each of which isstraight-chain or branched and has 1 to 6 carbon atoms in the alkylmoieties; and R¹³ represents hydrogen or straight-chain or branchedalkyl having 1 to 12 carbon atoms, which alkyl is mono- topentasubstituted, identically or differently, by halogen, cyano, amino,hydroxyl, mercapto, carboxyl, nitro, or alkoxy, alkylthio oralkoxycarbonyl, each of which is straight-chain or branched and has 1 to6 carbon atoms in the individual alkyl moieties.
 2. A method ofcontrolling undesired microorganisms, which method comprises applying tosuch undesired microorganisms or to their habitat a microbicidallyeffective amount of a dibromo-thiophene-carboxylic acid derivative ofthe formula ##STR48## in which R represents the groups --XR¹, --NR² R³,--NR⁴ OR⁵ and --NR⁴ --N(R⁵)₂,X represents oxygen or sulphur, R¹represents hydrogen,or straight-chain or branched alkyl having 1 to 12carbon atoms, which can be mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, carboxyl,nitro; alkoxy, alkylthio or alkoxycarbonyl, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms in theindividual alkyl moieties; and also the group --NR⁷ R⁸, or representsstraight-chain or branched alkenyl and alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or cycloalkyl having 3 to 7carbon atoms or cycloalkylalkyl having 3 to 7 carbon atoms in thecycloalkyl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkyl moiety, which is optionally substituted by cyano, wherethe cycloalkyl moiety of the two radicals mentioned can be mono- topentasubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms which is optionally mono-to trisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or tetrahydrofuran, tetrahydrothiophene,tetrahydropyran or tetrahydrothiopyran, where each of these radicals isoptionally mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, which isoptionally mono- to trisubstituted, identically or differently, by alkylhaving 1 to 4 carbon atoms, and/or by phenyl, which for its part isoptionally mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen andstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, or aryl having 6 to 10carbon atoms or aralkyl having 6 to 10 carbon atoms in the aryl moietyand 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety,which is optionally substituted by cyano, where each of the two radicalsin the aryl moiety can be mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched, each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl which for its part isoptionally mono- to trisubstituted, identically or differently, byhalogen and/or alkyl having 1 to 4 carbon atoms, or 5- or 6-memberedhetaryl or 5- or 6-membered hetarylalkyl having 1 to 6 carbon atoms inthe straight-chain or branched alkyl moiety, which is optionallysubstituted by cyano, where the hetaryl moiety in each case contains 1to 3 heteroatoms, selected from the group consisting of oxygen, sulphurand nitrogen, and which is optionally mono- to trisubstituted,identically or differently, by straight chain or branched alkyl having 1to 6 carbon atoms, halogen, cyano and/or straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms, R² and R³ are identical or different andrepresent hydrogen, or straight-chain or branched alkyl having 1 to 12carbon atoms, which can be mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, nitro,straight-chain or branched alkoxy having 1 to 6 carbon atoms,straight-chain or branched alkylthio having 1 to 6 carbon atoms and/orthe group ##STR49## or straight-chain or branched alkenyl or alkinylhaving 3 to 6 carbon atoms, each of which is optionally mono- topentasubstituted, identically or differently, by halogen, orcycloalkylhaving 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7 carbon atomsin the cycloalkyl moiety and 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, which is optionally substituted by cyano,where the cycloalkyl moiety of the two radicals mentioned are optionallymono- to pentasubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, optionally mono- totrisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part is optionally mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or tetrahydrofuran, tetrahydrothiophene,tetrahydropyran or tetrahydrothiopyran, where each of these radicals isoptionally mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, optionallymono- to trisubstituted, identically or differently, by alkyl having 1to 4 carbon atoms, and/or by phenyl, which for its part is optionallymono- to trisubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen and straight-chainor branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms, or aralkoxy having 6 or 10 carbonatoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chainor branched alkoxy moiety, optionally substituted by cyano, where thearyl moiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl, which for its part isoptionally mono- to trisubstituted, identically or differently, byhalogen and/or alkyl having 1 to 4 carbon atoms, R³ additionallyrepresents 5- or 6-membered hetaryl or 5- or 6-membered hetarylalkylhaving 1 to 6 carbon atoms in the straight-chain or branched alkylmoiety, optionally substituted by cyano, where the hetaryl moiety ineach case contains 1 to 3 heteroatoms and is optionally mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 6 carbon atoms, halogen, cyano and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, R² and R³ additionallytogether represent divalent alkanediyl having 2 to 6 CH₂ groups, where aCH₂ group is optionally replaced by O, S or NR⁶, R⁴ and R⁵ are identicalor different and represent hydrogen, or straight-chain or branched alkylhaving 1 to 12 carbon atoms, which is optionally mono- topentasubstituted, identically or differently, by halogen, cyano, amino,hydroxyl, mercapto, carboxyl, nitro; alkoxy, alkylthio oralkoxycarbonyl, each of which is straight-chain or branched, each having1 to 6 carbon atoms in the individual alkyl moieties; and also the group--NR⁷ R⁸, or straight-chain or branched alkenyl and alkinyl having 3 to6 carbon atoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, oraralkyl having 6 or 10 carbonatoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, optionally substituted by cyano, where thearyl moiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched, each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl, which for its part isoptionally mono- to trisubstituted, identically or differently, byhalogen and/or alkyl having 1 to 4 carbon atoms, R⁶ represents hydrogenand also alkyl and alkylcarbonyl, each of which is straight-chain orbranched, each having 1 to 6 carbon atoms in the alkyl moiety, R⁷represents straight-chain or branched alkyl having 1 to 6 carbon atoms,which is optionally mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, nitro,carboxyl; alkoxy and alkoxycarbonyl, each of which is straight-chain orbranched, each having 1 to 6 carbon atoms in the alkoxy moieties;alkylamino and dialkylamino having 1 to 6 carbon atoms in eachstraight-chain or branched alkyl moiety, orstraight-chain or branchedalkenyl or alkinyl each having 3 to 6 carbon atoms, each of which isoptionally substituted by 1 to 5 identical or different halogen atoms,or benzyl which in the phenyl moiety is optionally mono- totrisubstituted, identically or differently, by halogen, nitro, cyano,straight-chain or branched alkyl having 1 to 6 carbon atoms, and alsohalogenoalkyl, halogenoalkoxy or halogenoalkylthio, each of which isstraight-chain or branched, each having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms and R⁸ represents hydrogen, orstraight-chain or branched alkyl having 1 to 6 carbon atoms, which isoptionally mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, nitro, carboxyl; alkoxy andalkoxycarbonyl, each of which is straight-chain or branched, each having1 to 6 carbon atoms in the alkoxy moieties, alkylamino and dialkylaminohaving 1 to 6 carbon atoms in each straight-chain or branched alkylmoiety, orstraight-chain or branched alkenyl or alkinyl each having 3 to6 carbon atoms, each of which is optionally substituted by 1 to 5identical or different halogen atoms, or benzyl which in the phenylmoiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, nitro, cyano, straight-chain or branched alkylhaving 1 to 6 carbon atoms, and also halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms, or R⁷ and R⁸ additionally together represent divalent alkanediylhaving 4 to 6 CH₂ groups, it optionally being possible for a CH₂ groupto be replaced by O, S or NR⁶ and R⁶ having the meanings mentionedabove.
 3. The method as claimed in claim 2, wherein the microbicidallyactive compound is the dibromo-thiophene-carboxylic acid derivative ofthe formula ##STR50##
 4. The method as claimed in claim 2, wherein themicrobicidally active compound is the dibromo-thiophene-carboxylic acidderivative of the formula ##STR51##
 5. The method as claimed in claim 2,wherein the microbicidally active compound is thedibromo-thiophene-carboxylic acid derivative of the formula ##STR52## 6.A dibromo-thiophene-carboxylic acid derivative of the formula ##STR53##in which R⁹ represents the groups --OR¹⁰, ##STR54## R¹⁰ representsstraight-chain or branched alkyl having 1 to 12 carbon atoms, which ismono- to pentasubstituted, identically or differently, by halogen,cyano, amino, hydroxyl, mercapto, carboxyl, nitro; alkoxy, alkylthio oralkoxycarbonyl, each of which is straight-chain or branched, each having1 to 6 carbon atoms in the individual alkyl moieties; and also the group--NR⁷ R⁸, orrepresents straight-chain or branched alkenyl having 3 to 6carbon atoms, which is optionally mono- to pentasubstituted, identicallyor differently, by halogen, or cycloalkyl having 3 to 7 carbon atoms orcycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and1 to 4 carbon atoms in the straight-chain or branched alkyl moiety,which is optionally substituted by cyano, where the cycloalkyl moiety ofthe two radicals mentioned can be mono- to pentasubstituted, identicallyor differently, by straight-chain or branched alkyl having 1 to 4 carbonatoms, halogen, straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 identical or different halogen atoms, cyano,alkylenedioxo having 1 to 3 carbon atoms, cycloalkyl having 3 to 7carbon atoms which is optionally mono- to trisubstituted, identically ordifferently, by alkyl having 1 to 4 carbon atoms, and/or by phenyl,which for its part is optionally mono- to trisubstituted, identically ordifferently, by straight-chain or branched alkyl having 1 to 4 carbonatoms, halogen and straight-chain or branched halogenoalkyl having 1 to4 carbon atoms and 1 to 5 identical or different halogen atoms, ortetrahydrofuran, tetrahydrothiophene, tetrahydropyran ortetrahydrothiopyran, where each of these radicals is optionally mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, which is optionally mono-to trisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or aryl having 6 to 10 carbon atoms oraralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, which isoptionally substituted by cyano, where each of the two radicals in thearyl moiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched, each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl which for its part can bemono- to trisubstituted, identically or differently, by halogen and/oralkyl having 1 to 4 carbon atoms, or 5- or 6-membered hetaryl or 5- or6-membered hetarylalkyl having 1 to 6 carbon atoms in the straight-chainor branched alkyl moiety, which is optionally substituted by cyano,where the hetaryl moiety in each case contains 1 to 3 heteroatomsselected from the group consisting of oxygen, sulphur and nitrogen, andwhich is optionally mono- to trisubstituted, identically or differently,by straight-chain or branched alkyl having 1 to 6 carbon atoms, halogen,cyano and/or straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 identical or different halogen atoms, R¹¹ andR¹² are identical or different and represent straight-chain or branchedalkyl having 1 to 12 carbon atoms, which is mono- to pentasubstituted,identically or differently, by halogen, cyano, amino, hydroxyl,mercapto, nitro, straight-chain or branched alkoxy having 1 to 6 carbonatoms, straight-chain or branched alkylthio having 1 to 6 carbon atomsand/or the group ##STR55## or straight-chain or branched alkenyl oralkinyl having 3 to 6 carbon atoms, each of which is optionally mono- topentasubstituted, identically or differently, by halogen, orcycloalkylhaving 3 to 7 carbon atoms or cycloalkylalkyl having 3 to 7 carbon atomsin the cycloalkyl moiety and 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, which is optionally substituted by cyano,where the cycloalkyl moiety of the two radicals mentioned are optionallymono- to pentasubstituted, identically or differently, by straight-chainor branched alkyl having 1 to 4 carbon atoms, halogen, straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, cyano, alkylenedioxo having 1 to 3 carbonatoms, cycloalkyl having 3 to 7 carbon atoms, optionally mono- totrisubstituted, identically or differently, by alkyl having 1 to 4carbon atoms, and/or by phenyl, which for its part is optionally mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or tetrahydrofuran, tetrahydrothiophene,tetrahydropyran or tetrahydrothiopyran, where each of these radicals isoptionally mono- to trisubstituted, identically or differently, bystraight-chain or branched alkyl having 1 to 4 carbon atoms, halogen,straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, cyano, alkylenedioxo having1 to 3 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, optionallymono- to trisubstituted, identically or differently, by alkyl having 1to 4 carbon atoms, and/or by phenyl, which for its part can be mono- totrisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 4 carbon atoms, halogen and straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identicalor different halogen atoms, or aralkoxy having 6 or 10 carbon atoms inthe aryl moiety and 1 to 4 carbon atoms in the straight-chain orbranched alkoxy moiety, optionally substituted by cyano, where the arylmoiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl, which for its part can bemono- to trisubstituted, identically or differently, by halogen and/oralkyl having 1 to 4 carbon atoms, R¹² additionally represents 5- or6-membered hetaryl optionally substituted by cyano, where the hetarylmoiety in each case contains 1 to 3 heteroatoms and is optionally mono-to trisubstituted, identically or differently, by straight-chain orbranched alkyl having 1 to 6 carbon atoms, halogen, cyano and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 5 identical or different halogen atoms, or R¹¹ and R¹² togetherrepresent divalent alkanediyl having 2 to 6 CH₂ groups, where a CH₂group is optionally replaced by O, S or NR⁶, R⁴ and R⁵ are identical ordifferent and represent straight-chain or branched alkyl having 1 to 12carbon atoms, which is mono- to pentasubstituted, identically ordifferently, by halogen, cyano, amino, hydroxyl, mercapto, carboxyl,nitro; alkoxy, alkylthio or alkoxycarbonyl, each of which isstraight-chain or branched, each having 1 to 6 carbon atoms in theindividual alkyl moieties; and also the group --NR⁷ R⁸, orstraight-chain or branched alkenyl and alkinyl having 3 to 6 carbonatoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, R⁶ represents hydrogen and alsoalkyl and alkylcarbonyl, each of which is straight-chain or branched,each having 1 to 6 carbon atoms in the alkyl moiety; R⁷ representsstraight-chain or branched alkyl having 1 to 6 carbon atoms, which isoptionally mono- to pentasubstituted, identically or differently, byhalogen, cyano, amino, hydroxyl, mercapto, nitro, carboxyl; alkoxy andalkoxycarbonyl, each of which is straight-chain or branched, each having1 to 6 carbon atoms in the alkoxy moieties; alkylamino and dialkylaminohaving 1 to 6 carbon atoms in each straight-chain or branched alkylmoiety, orstraight-chain or branched alkenyl or alkinyl each having 3 to6 carbon atoms, each of which is optionally substituted by 1 to 5identical or different halogen atoms, or benzyl which in the phenylmoiety is optionally mono- to trisubstituted identically or differently,by halogen, nitro, cyano, straight-chain or branched alkyl having 1 to 6carbon atoms, and also halogenoalkyl, halogenoalkoxy orhalogenoalkylthio, each of which is straight-chain or branched, eachhaving 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms and R⁸ represents hydrogen, or straight-chain or branched alkylhaving 1 to 6 carbon atoms, which is optionally mono- topentasubstituted, identically or differently, by halogen, cyano, amino,hydroxyl, mercapto, nitro, carboxyl; alkoxy and alkoxycarbonyl, each ofwhich is straight-chain or branched, each having 1 to 6 carbon atoms inthe alkoxy moieties, alkylamino and dialkylamino having 1 to 6 carbonatoms in each straight-chain or branched alkyl moiety, orstraight-chainor branched alkenyl or alkinyl each having 3 to 6 carbon atoms, each ofwhich is optionally substituted by 1 to 5 identical or different halogenatoms, or benzyl which in the phenyl moiety is optionally mono- totrisubstituted, identically or differently, by halogen, nitro, cyano,straight-chain or branched alkyl having 1 to 6 carbon atoms, and alsohalogenoalkyl, halogenoalkoxy or halogenoalkylthio, each of which isstraight-chain or branched, each having 1 to 4 carbon atoms and 1 to 5identical or different halogen atoms, or R⁷ and R⁸ additionally togetherrepresent divalent alkanediyl having 4 to 6 CH₂ groups, it optionallybeing possible for a CH₂ group to be replaced by O, S or NR⁶ and R⁶having the meanings mentioned above, and R¹³ represents hydrogen, orstraight-chain or branched alkyl having 1 to 12 carbon atoms, which ismono- to pentasubstituted, identically or differently, by halogen,cyano, amino, hydroxyl, mercapto, carboxyl, nitro; alkoxy, alkylthio oralkoxycarbonyl, each of which is straight-chain or branched, each having1 to 6 carbon atoms in the individual alkyl moieties; and also the group--NR⁷ R⁸, orstraight-chain or branched alkenyl and alkinyl having 3 to 6carbon atoms, each of which is optionally mono- to pentasubstituted,identically or differently, by halogen, or aralkyl having 6 or 10 carbonatoms in the aryl moiety and 1 to 4 carbon atoms in the straight-chainor branched alkyl moiety, optionally substituted by cyano, where thearyl moiety is optionally mono- to trisubstituted, identically ordifferently, by halogen, hydroxyl, cyano, nitro; alkyl, alkoxy oralkylthio, each of which is straight-chain or branched, each having 1 to4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; halogenoalkyl,halogenoalkoxy or halogenoalkylthio, each of which is straight-chain orbranched, each having 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms; and/or by phenyl, which for its part isoptionally mono- to trisubstituted, identically or differently, byhalogen and/or alkyl having 1 to 4 carbon atoms.
 7. A microbicidalcomposition comprising a microbicidally effective amount of a compoundas claimed in claim 1 and an inert diluent.